John Kenney and Bill Landay
were best friends at Roxbury Latin School and shared a loathing for a certain English assignment, handed out each Friday and due back the following Monday. Students had to write a two-page essay on a given topic.

“The idea of those two pages to me was a Herculean task,” says Kenney. “I tried to write in very large script.” As for Landay, he’d put off the writing until the last minute on Sunday night.

Today, they laugh at the memories and the irony. Those fearful essayists turned into authors, Landay with three award-winning crime novels, and Kenney with his first novel, “Truth in Advertising,” published in January to starred reviews and featured as an Amazon Book of the Month.

Set in the New York advertising world, Kenney’s book was recently praised in The New York Times as a debut that “offers a pleasing lightness-to-heart ratio.”

For years, Kenney and Landay have been each other’s sounding board on life, and on writing. Before giving a presentation at the Boston Public Library recently, the friends worried whether anyone would show up.

‘[Writing is] a struggle every day.’

“There will be three homeless people and some guy who keeps saying, ‘Larry! Larry! Larry!’ ” Kenney quips. He’s a funny guy, and much of his humor is aimed at himself.

But not to worry. A few hours later, their presentation is delayed while library workers set up more chairs for the overflow crowd of about 150. And no one yells “Larry! Larry! Larry!”

Landay grew up in Brookline, Kenney in West Roxbury. Kenney, who graduated from UMass-Amherst, worked for the Hill Holliday advertising agency in Boston before moving to New York, where he worked for Ogilvy & Mather. Landay went to Yale and got a law degree from Boston College before joining the Middlesex County District Attorney’s Office.

Their books are based on their work experiences, Landay with seven years in criminal prosecution, Kenney with 17 in advertising. At the BPL, Kenney reads a passage about a New York advertising team pitching a petroleum company, evoking laughter from the audience.

“This is actually my second first novel,” Kenney tells the crowd. “I think the reason the first one didn’t work is that it was long, incredibly depressing, and there was no plot.” More laughter. At Landay’s suggestion, the novel was deep-sixed in a drawer.

Landay is on the stage with Kenney, asking and soliciting questions about “Truth in Advertising.” Both on and off stage, the friends are one another’s biggest fans. “ ‘Truth in Advertising’ has the marks of a breakout book,” Landay tells the audience. “There is buzz around this book and it’s incredibly exciting.”

Over lunch at the Oak Long Bar + Kitchen at the Fairmont Copley Plaza, Kenney similarly gushed over Landay’s most recent novel, “Defending Jacob,” noting that it “debuted at No. 4 on The New York Times bestseller list, and it was on there for nine months.” The plot involves an assistant district attorney whose teenage son is accused of murdering a classmate in Newton.

Landay points out that the opening scene in his second novel, “The Strangler,” was set in this exact spot, the old Oak Room at what was then the Copley Plaza hotel. “The guy has a drink here, then goes upstairs and robs a room,” says Landay. (Yes, “the guy” is based on the Boston Strangler.)

In 1996, it was Kenney in whom Landay confided that he was hoping to leave the DA’s office to write books. Kenney was impressed, and encouraging.

For the next two years, then District Attorney Tom Reilly let Landay work part-time; Landay left for good in 1998. In 2003, his first novel, “Mission Flats,” won a Dagger Award for best first crime novel.

Meanwhile, in 1995, Kenney moved to New York. Landay had helped move him “in a rented U-Haul with the 14 things I owned,” says Kenney, who planned to return to Boston in two years.

Landay knew better: “You’re never coming back,” he told his friend.

Kenney is still living in New York, where he met his wife. The couple live in Brooklyn Heights and have a 4-year-old daughter and an 8-month-old son. They have a small place on the Cape, and vacation there every summer. Kenney’s five brothers live in Massachusetts; the oldest, Charles, is a former Globe reporter and editor who left in 1994 and has written 12 books.

At Ogilvy, John Kenney wrote TV commercials and print ads for AmEx, British Petroleum, and AT&T, among other accounts. He also freelanced columns for various newspapers and magazines, and has been a contributor to The New Yorker since 1999.

In 2009, during the recession, Kenney was laid off by his advertising firm; it was a good time to start a novel. He had an idea, and took “a few thousand” words from his earlier manuscript still in that drawer. “Truth in Advertising” was born.

Associated Press

Kenney’s first novel, “Truth in Advertising,” was published in January.

At lunch, Kenney is asked how it feels to be a novelist. “I’m not sure you can call yourself a novelist with just one book,” he replies.

“Sure you can,” says Landay. “So Harper Lee’s not a novelist?” Lee’s only book, “To Kill a Mockingbird,” won the Pulitzer Prize in 1961 and has sold more than 30 million copies in 18 languages.

The question leads the men into a discussion on the challenge of writing, how Philip Roth, upon recently retiring after writing 31 books, put up a Post-it note in his apartment: “The struggle with writing is over.”

“It’s a struggle every day,” says Landay.

Kenney agrees: “Every day, you learn how little you know, trying to develop a story, a character, a fresh perspective.”

At the library that night, Kenney squints and spots a familiar face in the crowd. “I see Joe Kerner,” he says. “He taught English at Roxbury Latin. I think it’s fair to say, Joe, that I was the worst student you ever had.” Afterward, the retired English teacher compliments both men on their success.

But high school was a tough time for Kenney. His mother died the year before he entered, leaving his firefighter dad with six sons. Kenney had attended Boston public schools during the turmoil of desegregation, and felt ill prepared for the rigors of Roxbury Latin.

So it was with mixed emotions that he returned recently, with Landay, to speak to a senior English class. The alums also got a tour of the school that they had last toured as hopeful 13-year-olds. Kenney remarks “how nothing has changed, how everything has changed.”

He quips: “They made us both take the entrance exam again, and we failed.”